6692-89-3

Basic information

• Product Name: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine
• Synonyms: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine;N5-Carbamoyl-N2-[(benzyloxy)carbonyl]-L-ornithine;(S)-2-(((Benzyloxy)carbonyl)amino)-5-ureidopentanoic acid;Na-Benzyloxycarbonyl-L-citrulline
• CAS NO: 6692-89-3
• Molecular Formula: C₁₄H₁₉N₃O₅
• Molecular Weight: 309.31776
• EINECS: 229-736-2
• Mol File: 6692-89-3.mol

Chemical Properties

• Boiling Point: 569.6°C at 760 mmHg
• Flash Point: 298.3°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 8.17E-14mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine(CAS DataBase Reference)
• NIST Chemistry Reference: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine(6692-89-3)
• EPA Substance Registry System: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine(6692-89-3)

Safety Data

• Hazardous Substances Data: 6692-89-3(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine is used as a research compound for studying its properties and interactions with biological systems, potentially leading to insights into ornithine-related metabolic pathways and mechanisms.
Used in Pharmaceutical Development:
N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine is used as a potential drug candidate for the development of new therapeutic agents, given its unique structural features and possible biological effects, which may be harnessed for treating specific diseases or conditions.
Used in Drug Delivery Systems:
In the pharmaceutical industry, N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine may be utilized as a component in drug delivery systems, potentially enhancing the efficacy and bioavailability of other therapeutic agents by improving their solubility, stability, or targeted delivery.
Used in Diagnostic Applications:
N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine could be employed in the development of diagnostic tools or assays, where its unique chemical properties may be leveraged for detecting or monitoring specific biological processes or conditions related to ornithine metabolism.

InChI:InChI=1/C14H19N3O5/c15-13(20)16-8-4-7-11(12(18)19)17-14(21)22-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,17,21)(H,18,19)(H3,15,16,20)/t11-/m0/s1

Upstream product

• 372-75-8 Citrulline 
• 372-75-8 2-Amino-5-ureido-pentanoic acid 
• 501-53-1 benzyl chloroformate 
• 3184-13-2 L-ornithine hydrochloride 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 122702-26-5 N-(N²-benzyloxycarbonyl-N⁵-carbamoyl-L-ornithyl)-L-glutamic acid dibenzyl ester 
• 89499-13-8 methyl N^α-benzyloxycarbonyl-L-citrullinate 
• 89499-13-8 N^α-(benzyloxycarbonyl)-L-citrulline methyl ester 
• 587-90-6 bis-N,N'-(4-nitrophenyl)urea 
• 38150-56-0 3-(benzyloxycarbonylamido)-piperidin-2-one 
• 83575-38-6 N₁-carbamoyl-3-benzyloxycarbonylamidopiperidin-2-one 
• 83575-37-5 Nα-benzyloxycarbonyl-L-citrulline p-nitroanilide 
• 89499-14-9 methyl N^α-benzyloxycarbonyl-N^ω-carbamoyl-L-citrullinate 
• 83575-44-4 benzyloxycarbonyl-L-prolyl-L-citrulline p-nitroanilide 
• 83575-46-6 benzyloxycarbonylglycyl-L-prolyl-L-citrulline p-nitroanilide 
• 83575-45-5 L-prolyl-L-citrulline p-nitroanilide hydrobromide 
• 83575-47-7 benzyloxycarbonyl-D-phenylalanyl-L-prolyl-L-citrulline p-nitroanilide 
• 125735-05-9 N^α-(benzyloxycarbonyl)-N^δ-cyanoornithine methyl ester 
• 125735-10-6 2-Benzyloxycarbonylamino-5-(5-methoxycarbonylmethyl-4-oxo-4,5-dihydro-1H-imidazol-2-ylamino)-pentanoic acid methyl ester 

Relevant articles and documents

Improved Methodology for the Synthesis of a Cathepsin B Cleavable Dipeptide Linker, Widely Used in Antibody-Drug Conjugate Research

Antibody-drug conjugates (ADCs) represent an emerging class of biopharmaceutical agents that deliver highly potent anticancer agents (payloads) selectively to tumors or components associated with the tumor microenvironment. The linker, responsible for the connection between the antibody and payload, is a crucial component of ADCs. In certain examples the linker is composed of a cleavable short peptide which imparts an additional aspect of selectivity. Especially prevalent is the cathepsin B cleavable Mc-Val-Cit-PABOH linker utilized in many pre-clinical ADC candidates, as well as the FDA approved ADC ADCETRIS (brentuximab vedotin). An alternative route for the synthesis of the cathepsin B cleavable Mc-Val-Cit-PABOH linker is reported herein that involved six steps from l-Citrulline and proceeded with a 50% overall yield. In this modified route, the spacer (a para-aminobenzyl alcohol moiety) was incorporated via HATU coupling followed by dipeptide formation. Importantly, this route avoided undesirable epimerization and proceeded with improved overall yield. Utilizing this methodology, a drug-linker construct incorporating a potent small-molecule inhibitor of tubulin polymerization (referred to as KGP05), was synthesized as a representative example.

Urea cycle: Chemical simulation of arginine biosynthesis

We have successfully simulated the salient features of the urea cycle. In this effort an appropriately protected ornithine was transformed to citrulline, via use of a novel amide transfer reagent; the citrulline, in turn, was converted into argininosuccinate which necessitated a new activation procedure to enable acceptance of dimethyl aspartate. Fragmentation of argininosuccinate under carefully controlled conditions afforded arginine. The final step in the cycle, namely, the hydrolysis of arginine to urea and ornithine, has already been accomplished. Amino group transfer from aspartate has also been demonstrated in the conversion of hypoxanthine to adenine.